A fan of Fiddler on the Roof, Lizzy has always been curious about modern-day matchmakers. So, TOC hooked her up with two: Stefanie Safran of Chicago-based Stef and the City and Janis Spindel, a New Yorker entering the Chicago market.

December 18 Today I met Stefanie Safran, one of my matchmakers for the next month, at the 24-hour Starbucks in Old Town. In 90 minutes, I disclosed more personal details about my dating history and preferences than a stranger (or even friend) should ever want to know. Stef was energetic, and eager not to pigeonhole herself into the matchmaker category. Instead, she calls herself “Chicago’s Introductionista,” meaning she also gives clients tips on how to meet dates. She suggested I create an account with meetup.com and join several LinkedIn groups, including the Northwestern alumni group, and join her at the gym so I could watch her hit on guys. I was afraid to mention that I wear old T-shirts to the gym and have my headphones in at all times.

I learned Stef has serious rules regarding her clients, including how they are to meet for their first date (guy must call girl and arrange the date near her house) and communicate (for the first three weeks, phone calls only!). If someone breaks any of her 16 rules, Stef keeps at least part of the $25 deposit they’ve paid, on top of her $42–$125 base fee per introduction. I left the meeting feeling positive, if for no other reason than Stef said I didn’t need the staged date—a service in which she would send me out with one of her colleagues and later critique me. Scary.

December 20 I received an e-mail from Club J-Love, the women’s division of dating services offered by Janis Spindel, apparently one of the more prominent matchmakers in the U.S. Who knew there were famous matchmakers? But when I mentioned Janis’s name, Stef knew her immediately. A woman who later told me she’s really the only person in the country who has the gift of matching people for lasting marriage, Janis charges women $25 to submit a one-page profile, along with two pictures, to her “club.” If you meet the requirements of what her pool of men is looking for, you’re then eligible to attend a group meeting with Janis ($200), or arrange a one-on-one consultation ($1,000). I resisted the urge to send a Halloween photo of myself and a few friends dressed in head-to-toe Broadway Cats gear as the “body shot” she requires. I assume the men who pay her between $100,000 and $500,000 (no joke) to find them wives want more refinement than spandex and face paint. Although in my book, anyone who really commits to a costume is golden.

December 22 Stef sent me for a makeover with Joey Kiening at Solo Salon in the West Loop, who charges $35–$95 for a style and $55 for a makeup job. He did a beautiful, natural job on both my hair and makeup. My fear that I would end up looking like a tranny-Kardashian went unfounded.

On the way to the salon, Janis left me a message about the beyond adorable young man looking for a wife who she just had lunch with at the Modern. I don’t think she saw him as a prospect for me, but she does ask her clients to be open to meeting men from other cities who would fly in for dates. When I called her back, she told me (1) my hair is not sexy enough, and (2) I’m a tough case, since I’m 5'10". I responded that for all my years of middle-school slouching, I’m quite happy with my height. And for the record, I have good hair and an even better stylist—more than a few of my friends have gone to see Jason Fanning at Art + Science on Halsted after complimenting one or another of my cuts.

After the makeover, it was off to meet Stef for a networking party at Excalibur. I have never been to Excalibur. Stef called this her “Wing Chix” experience: Throughout the night, she brought over men and introduced them, though few seemed interested in anything beyond a business-card swap. I had one entertaining exchange with a guy from Wisconsin, but he visibly panicked that I might include his name in this diary, which I told him about after Stef informed him I’m her client. After we took advantage of the “red carpet” photographer, making him take photos of us in a fake fistfight, I left the event and went to Logan Square to meet friends for bourbon and burritos late into the night.

December 24 Stef sent me an e-mail with her take on the Excalibur event. She thinks I might be too picky (friends have told me this), and thinks the guy from the end of the night was either shy, just interested in networking or needed time to get to know me on a “best friend” level before he would want to date. I think he’s simply creeped out by being hit on by a matchmaker and her charge at a networking event. The e-mail included suggestions on how to improve my Match profile, including taking down a photo of me with the pumpkin I carved of FrankenRahm (our mayor as Frankenstein, duh!) last year. “Your face looks shiny,” she wrote. I think guys would see that photo and think: Your pumpkin looks awesome. But I took her suggestions…most of them. I can’t bear to use as many exclamation points as she wants.

December 28 Yielding to advice from friends, I sent a two-line e-mail to the guy from Excalibur. Even if he doesn’t reply, he should get a laugh out of the fistfight photos.

January 11 Stef, who is on a singles trip to Europe, e-mails me to say she is going to set me up with an Abercrombie model. My entire family’s reaction: “She knows an Abercrombie model who’s not gay?”

January 18 As Stef requested, I’ve joined several online meetup and LinkedIn groups, but I haven’t yet gone to any events. I grew up here and don’t have trouble keeping a full social schedule, so it’s hard for me to give up friend time to go meet strangers by myself.

Sadly, this month-long matchmaking experience didn’t include any actual matching. Janis wanted to come to Chicago and go “galavanting in that triangle area” (shudder) or to a high-end charity event. Neither worked out with our schedules before the month was over, so I doubt I will ever meet any of her wealthy, lonely clients. Stef’s Abercrombie model has yet to materialize, and the Excalibur dude, as I suspected, never replied. Perhaps conducting this experiment over the holidays wasn’t the right time of year. Or maybe Janis was right, and as soon as I figure out how to pull off “sexy hair,” I’ll settle down with a beyond adorable man. I think I’ll take my chances—and bet on finding someone, sans matchmaker, who appreciates my height, style and pumpkin-carving skills.